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Erschienen in: Journal of Natural Medicines 2/2023

10.12.2022 | Note

A new 1,2-diketone physalin isolated from Physalis minima and TRAIL-resistance overcoming activity of physalins

verfasst von: Teruhisa Manome, Yasumasa Hara, Masami Ishibashi

Erschienen in: Journal of Natural Medicines | Ausgabe 2/2023

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Abstract

A new 1,2-diketone physalin, physalin XII (1), and 13 known compounds were isolated from the methanol extract of Physalis minima whole plant collected in Thailand. Among them, five physalins (26) had tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-resistance overcoming activity, and physalin F (3) was the most active with an IC50 value of 0.39 µM against human gastric adenocarcinoma cell line AGS in the presence of TRAIL (100 ng/mL). An investigation of the TRAIL-resistance overcoming activity of physalins using western blot analysis showed that 3 promoted TRAIL-induced apoptosis by suppressing anti-apoptotic proteins c-FLIP and Bcl-2.
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Literatur
1.
Zurück zum Zitat Matsuura T, Kawai M, Nakashima R, Butsugan Y (1970) Structures of physalin A and physalin B, 13,14-seco-16,24-cyclo-steroids from Physalis alkekengi var. Francheti J Chem Soc Perkin Trans 15:664–670 Matsuura T, Kawai M, Nakashima R, Butsugan Y (1970) Structures of physalin A and physalin B, 13,14-seco-16,24-cyclo-steroids from Physalis alkekengi var. Francheti J Chem Soc Perkin Trans 15:664–670
2.
Zurück zum Zitat Wu J, Zhao J, Zhang T, Gu Y, Khan I, Zou Z, Xu Q (2021) Naturally occurring physalins from the genus Physalis: a review. Phytochemistry 191:112925CrossRefPubMed Wu J, Zhao J, Zhang T, Gu Y, Khan I, Zou Z, Xu Q (2021) Naturally occurring physalins from the genus Physalis: a review. Phytochemistry 191:112925CrossRefPubMed
3.
Zurück zum Zitat Yang YK, Xie SD, Xu WX, Nian Y, Liu XL, Peng XR, Ding ZT, Qiu MH (2016) Six new physalins from Physalis alkekengi var. franchetii and their cytotoxicity and antibacterial activity. Fitoterapia 112:144–152CrossRefPubMed Yang YK, Xie SD, Xu WX, Nian Y, Liu XL, Peng XR, Ding ZT, Qiu MH (2016) Six new physalins from Physalis alkekengi var. franchetii and their cytotoxicity and antibacterial activity. Fitoterapia 112:144–152CrossRefPubMed
4.
Zurück zum Zitat Sun CP, Qiu CY, Zhao F, Kang N, Chen LX, Qiu F (2017) Physalins V-IX, 16,24-cyclo-13,14-seco withanolides from Physalis angulata and their antiproliferative and anti-inflammatory activities. Sci Rep 7:4057CrossRefPubMedPubMedCentral Sun CP, Qiu CY, Zhao F, Kang N, Chen LX, Qiu F (2017) Physalins V-IX, 16,24-cyclo-13,14-seco withanolides from Physalis angulata and their antiproliferative and anti-inflammatory activities. Sci Rep 7:4057CrossRefPubMedPubMedCentral
5.
Zurück zum Zitat Jacobo-Herrera NJ, Bremner P, Márquez N, Gupta MP, Gibbons S, Muñoz E, Heinrich M (2006) Physalins from Witheringia solanacea as modulators of the NF-κB cascade. J Nat Prod 69:328–331CrossRefPubMed Jacobo-Herrera NJ, Bremner P, Márquez N, Gupta MP, Gibbons S, Muñoz E, Heinrich M (2006) Physalins from Witheringia solanacea as modulators of the NF-κB cascade. J Nat Prod 69:328–331CrossRefPubMed
6.
Zurück zum Zitat Arai MA, Uchida K, Sadhu SK, Ahmed F, Ishibashi M (2014) Physalin H from Solanum nigrum as Hh signaling inhibitor blocks GLI1-DNA complex formation. Beil J Org Chem 10:134–140CrossRef Arai MA, Uchida K, Sadhu SK, Ahmed F, Ishibashi M (2014) Physalin H from Solanum nigrum as Hh signaling inhibitor blocks GLI1-DNA complex formation. Beil J Org Chem 10:134–140CrossRef
7.
Zurück zum Zitat Hosoya T, Arai MA, Koyano T, Kowithayakorn T, Ishibashi M (2008) Naturally occurring small-molecule inhibitors of Hedgehog/GLI-mediated transcription. ChemBioChem 9:1082–1092CrossRefPubMed Hosoya T, Arai MA, Koyano T, Kowithayakorn T, Ishibashi M (2008) Naturally occurring small-molecule inhibitors of Hedgehog/GLI-mediated transcription. ChemBioChem 9:1082–1092CrossRefPubMed
8.
Zurück zum Zitat Jitrangsri K, Takaya A, Hara Y, Sadhu SK, Ahmed F, Ishibashi M (2021) Bioactivity-guided isolation of TRAIL-resistance overcoming activity compounds from the leaves of Murraya exotica. Nat Prod Commun 16:1934578X211065843 Jitrangsri K, Takaya A, Hara Y, Sadhu SK, Ahmed F, Ishibashi M (2021) Bioactivity-guided isolation of TRAIL-resistance overcoming activity compounds from the leaves of Murraya exotica. Nat Prod Commun 16:1934578X211065843
9.
Zurück zum Zitat Manome T, Hara Y, Ahmed F, Sadhu SK, Ishibashi M (2022) Thannilignan glucoside and 2-(β-glucopyranosyl)-3-isoxazolin-5-one derivative, two new compounds isolated from Terminalia bellirica. J Nat Med 76:482–489CrossRefPubMed Manome T, Hara Y, Ahmed F, Sadhu SK, Ishibashi M (2022) Thannilignan glucoside and 2-(β-glucopyranosyl)-3-isoxazolin-5-one derivative, two new compounds isolated from Terminalia bellirica. J Nat Med 76:482–489CrossRefPubMed
10.
Zurück zum Zitat von Karstedt S, Montinaro A, Walczak H (2017) Exploring the TRAILs less travelled: TRAIL in cancer biology and therapy. Nat Rev Cancer 17:352–366CrossRef von Karstedt S, Montinaro A, Walczak H (2017) Exploring the TRAILs less travelled: TRAIL in cancer biology and therapy. Nat Rev Cancer 17:352–366CrossRef
11.
Zurück zum Zitat Makino B, Kawai M, Iwata Y, Yamamura H, Butsugan Y, Ogawa K, Hayashi M (1995) Physalins possessing an endoperoxy structure from Physalis alkekengi var. francheti. structural revision of physalin K. Bull Chem Soc Jpn 68:219–226CrossRef Makino B, Kawai M, Iwata Y, Yamamura H, Butsugan Y, Ogawa K, Hayashi M (1995) Physalins possessing an endoperoxy structure from Physalis alkekengi var. francheti. structural revision of physalin K. Bull Chem Soc Jpn 68:219–226CrossRef
12.
Zurück zum Zitat Kawai M, Makino B, Taga T, Miwa Y, Yamamoto T, Furuta T, Yamamura H, Butsugan Y, Ogawa K, Hayashi M (1994) Crystal structures of 5α,6α-epoxy and 2,3-dihydro derivatives of physalin B, a 13,14-seco-16,24-cyclosteroid, and their 1H NMR spectral analysis. Bull Chem Soc Jpn 67:222–226CrossRef Kawai M, Makino B, Taga T, Miwa Y, Yamamoto T, Furuta T, Yamamura H, Butsugan Y, Ogawa K, Hayashi M (1994) Crystal structures of 5α,6α-epoxy and 2,3-dihydro derivatives of physalin B, a 13,14-seco-16,24-cyclosteroid, and their 1H NMR spectral analysis. Bull Chem Soc Jpn 67:222–226CrossRef
13.
Zurück zum Zitat Choudhary MI, Samreen SY, Shah SAA, Ahmed S, Rahman A (2006) Biotransformation of physalin H and leishmanicidal activity of its transformed products. Chem Pharm Bull 54:927–930CrossRef Choudhary MI, Samreen SY, Shah SAA, Ahmed S, Rahman A (2006) Biotransformation of physalin H and leishmanicidal activity of its transformed products. Chem Pharm Bull 54:927–930CrossRef
14.
Zurück zum Zitat Makino B, Kawai M, Ogura T, Nakanishi M, Yamamura H, Butsugan Y (1995) Structural revision of physalin H isolated from Physalis angulata. J Nat Prod 58:1668–1674CrossRef Makino B, Kawai M, Ogura T, Nakanishi M, Yamamura H, Butsugan Y (1995) Structural revision of physalin H isolated from Physalis angulata. J Nat Prod 58:1668–1674CrossRef
15.
Zurück zum Zitat Row LR, Reddy KS, Sarma NS, Matsuura T, Nakashima R (1980) New physalins from Physalis angulata and Physalis lancifolia. Structure and reactions of physalins D, I G and K. Phytochemistry 19:1175–1181CrossRef Row LR, Reddy KS, Sarma NS, Matsuura T, Nakashima R (1980) New physalins from Physalis angulata and Physalis lancifolia. Structure and reactions of physalins D, I G and K. Phytochemistry 19:1175–1181CrossRef
16.
Zurück zum Zitat Januário AH, Filho ER, Pietro RCLR, Kashima S, Sato DN, França SC (2002) Antimycobacterial physalins from Physalis angulata L. (Solanaceae). Phytother Res 16:445–448CrossRefPubMed Januário AH, Filho ER, Pietro RCLR, Kashima S, Sato DN, França SC (2002) Antimycobacterial physalins from Physalis angulata L. (Solanaceae). Phytother Res 16:445–448CrossRefPubMed
17.
Zurück zum Zitat Catalán CAN, de Heluani CS, Kotowicz C, Gedris TE, Herz W (2003) A linear sesterterpene, two squalene derivatives and two peptide derivatives from Croton hieronymi. Phytochemistry 64:625–629CrossRefPubMed Catalán CAN, de Heluani CS, Kotowicz C, Gedris TE, Herz W (2003) A linear sesterterpene, two squalene derivatives and two peptide derivatives from Croton hieronymi. Phytochemistry 64:625–629CrossRefPubMed
18.
Zurück zum Zitat Kai H, Baba M, Okuyama T (2007) Two new megastigmanes from the leaves of Cucumis sativus. Chem Pharm Bull 55:133–136CrossRef Kai H, Baba M, Okuyama T (2007) Two new megastigmanes from the leaves of Cucumis sativus. Chem Pharm Bull 55:133–136CrossRef
19.
Zurück zum Zitat Kimura J, Maki N (2002) New loliolide derivatives from the brown alga Undaria pinnatifida. J Nat Prod 65:57–58CrossRefPubMed Kimura J, Maki N (2002) New loliolide derivatives from the brown alga Undaria pinnatifida. J Nat Prod 65:57–58CrossRefPubMed
20.
Zurück zum Zitat Hammami S, Jannet HB, Bergaoui A, Ciavatta L, Cimino G, Mighri Z (2004) Isolation and structure elucidation of a flavanone, a flavanone glycoside and vomifoliol from Echiochilon fruticosum growing in Tunisia. Molecules 9:602–608CrossRefPubMedPubMedCentral Hammami S, Jannet HB, Bergaoui A, Ciavatta L, Cimino G, Mighri Z (2004) Isolation and structure elucidation of a flavanone, a flavanone glycoside and vomifoliol from Echiochilon fruticosum growing in Tunisia. Molecules 9:602–608CrossRefPubMedPubMedCentral
21.
Zurück zum Zitat Piggott L, Omidvar N, Pérez SM, Eberl M, Clarkson RW (2011) Suppression of apoptosis inhibitor c-FLIP selectively eliminates breast cancer stem cell activity in response to the anti-cancer agent, TRAIL. Breast Cancer Res 13:2–15CrossRef Piggott L, Omidvar N, Pérez SM, Eberl M, Clarkson RW (2011) Suppression of apoptosis inhibitor c-FLIP selectively eliminates breast cancer stem cell activity in response to the anti-cancer agent, TRAIL. Breast Cancer Res 13:2–15CrossRef
23.
24.
Zurück zum Zitat Walczak H, Bouchon A, Stahl H, Krammer PH (2000) Tumor necrosis factor-related apoptosis-inducing ligand retains its apoptosis-inducing capacity on Bcl-2- or Bcl-xL-overexpressing chemotherapy-resistant tumor cells. Cancer Res 60:3051–3057PubMed Walczak H, Bouchon A, Stahl H, Krammer PH (2000) Tumor necrosis factor-related apoptosis-inducing ligand retains its apoptosis-inducing capacity on Bcl-2- or Bcl-xL-overexpressing chemotherapy-resistant tumor cells. Cancer Res 60:3051–3057PubMed
25.
Zurück zum Zitat Kump E, Ji J, Wernli M, Hausermann P, Erb P (2008) Gli2 upregulates cFlip and renders basal cell carcinoma cells resistant to death ligand-mediated apoptosis. Oncogene 27:3856–3864CrossRefPubMed Kump E, Ji J, Wernli M, Hausermann P, Erb P (2008) Gli2 upregulates cFlip and renders basal cell carcinoma cells resistant to death ligand-mediated apoptosis. Oncogene 27:3856–3864CrossRefPubMed
26.
Zurück zum Zitat Regl G, Kasper M, Schnidar H, Eichberger T, Neill GW, Philpott MP, Esterbauer H, Hauser-Kronberger C, Frischauf AM, Aberger F (2004) Activation of the BCL2 promoter in response to Hedgehog/GLI signal transduction is predominantly mediated by GLI2. Cancer Res 64:7724–7731CrossRefPubMed Regl G, Kasper M, Schnidar H, Eichberger T, Neill GW, Philpott MP, Esterbauer H, Hauser-Kronberger C, Frischauf AM, Aberger F (2004) Activation of the BCL2 promoter in response to Hedgehog/GLI signal transduction is predominantly mediated by GLI2. Cancer Res 64:7724–7731CrossRefPubMed
27.
Zurück zum Zitat Zhang D, Liu J, Wang Y, Chen J, Chen T (2011) shRNA-mediated silencing of Gli2 gene inhibits proliferation and sensitizes human hepatocellular carcinoma cells towards TRAIL-induced apoptosis. J Cell Biochem 112:3140–3150CrossRefPubMed Zhang D, Liu J, Wang Y, Chen J, Chen T (2011) shRNA-mediated silencing of Gli2 gene inhibits proliferation and sensitizes human hepatocellular carcinoma cells towards TRAIL-induced apoptosis. J Cell Biochem 112:3140–3150CrossRefPubMed
28.
Zurück zum Zitat Zhang D, Li H, Lau W, Cao L, Li Y, Jiang X, Yang X, Xue P (2014) Gli2 silencing enhances TRAIL-induced apoptosis and reduces tumor growth in human hepatoma cells in vivo. Cancer Biol Ther 15:1667–1676CrossRefPubMedPubMedCentral Zhang D, Li H, Lau W, Cao L, Li Y, Jiang X, Yang X, Xue P (2014) Gli2 silencing enhances TRAIL-induced apoptosis and reduces tumor growth in human hepatoma cells in vivo. Cancer Biol Ther 15:1667–1676CrossRefPubMedPubMedCentral
29.
Zurück zum Zitat Lindhagen E, Nygren P, Larsson R (2008) The fluorometric microculture cytotoxicity assay. Nat Protoc 3:1364–1369CrossRefPubMed Lindhagen E, Nygren P, Larsson R (2008) The fluorometric microculture cytotoxicity assay. Nat Protoc 3:1364–1369CrossRefPubMed
Metadaten
Titel
A new 1,2-diketone physalin isolated from Physalis minima and TRAIL-resistance overcoming activity of physalins
verfasst von
Teruhisa Manome
Yasumasa Hara
Masami Ishibashi
Publikationsdatum
10.12.2022
Verlag
Springer Nature Singapore
Erschienen in
Journal of Natural Medicines / Ausgabe 2/2023
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-022-01670-x

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